JPH0334964A - デスフェリオキサミンｂ及びその類似体の合成方法 - Google Patents

デスフェリオキサミンｂ及びその類似体の合成方法

Info

Publication number: JPH0334964A
Authority: JP; Japan
Prior art keywords: formula; integer; compound; chemical; formulas
Prior art date: 1988-05-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP15204489A

Other languages

English (en)

Japanese (ja)

Inventor

Raymond J Bergeron

レイモンド　ジェイ　バージェロン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Florida

Original Assignee

University of Florida

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-05-17

Filing date

1989-06-14

Publication date

1991-02-14

1989-05-17 Priority claimed from US07/352,917 external-priority patent/US4987253A/en

1989-06-14 Application filed by University of Florida filed Critical University of Florida

1991-02-14 Publication of JPH0334964A publication Critical patent/JPH0334964A/ja

Status Pending legal-status Critical Current

Links

230000015572 biosynthetic process Effects 0.000 title description 9
238000003786 synthesis reaction Methods 0.000 title description 7
239000000126 substance Substances 0.000 claims abstract description 53
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 46
150000001412 amines Chemical class 0.000 claims abstract description 35
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
125000003118 aryl group Chemical group 0.000 claims abstract description 23
125000006239 protecting group Chemical group 0.000 claims abstract description 19
150000002825 nitriles Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 17
150000002923 oximes Chemical class 0.000 claims abstract description 12
150000008065 acid anhydrides Chemical class 0.000 claims abstract description 11
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 76
125000004432 carbon atom Chemical group C* 0.000 claims description 29
UBQYURCVBFRUQT-UHFFFAOYSA-N N-benzoyl-Ferrioxamine B Chemical compound CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN UBQYURCVBFRUQT-UHFFFAOYSA-N 0.000 claims description 18
-1 e.g. Chemical group 0.000 claims description 10
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims description 8
230000002194 synthesizing effect Effects 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
238000001308 synthesis method Methods 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
229940100198 alkylating agent Drugs 0.000 claims 3
239000002168 alkylating agent Substances 0.000 claims 3
208000002903 Thalassemia Diseases 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000000047 product Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 11
150000001408 amides Chemical class 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
239000002738 chelating agent Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
FNEARBHZFXEPFD-UHFFFAOYSA-N 5-oxopentanenitrile Chemical compound O=CCCCC#N FNEARBHZFXEPFD-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000000499 gel Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
229960000958 deferoxamine Drugs 0.000 description 4
239000003446 ligand Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229940014800 succinic anhydride Drugs 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
241000951471 Citrus junos Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000187747 Streptomyces Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
ZIPLUEXSCPLCEI-UHFFFAOYSA-N iminomethylideneazanide Chemical compound [NH-]C#N ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 3
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
JSAWFGSXRPCFSW-UHFFFAOYSA-N 5-chloropentanenitrile Chemical compound ClCCCCC#N JSAWFGSXRPCFSW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical group [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
208000002972 Hepatolenticular Degeneration Diseases 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
ZMXDDKWLCZADIW-YYWVXINBSA-N N,N-dimethylformamide-d7 Chemical compound [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 description 2
208000018839 Wilson disease Diseases 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
NLXXVSKHVGDQAT-UHFFFAOYSA-N o-(oxan-2-yl)hydroxylamine Chemical compound NOC1CCCCO1 NLXXVSKHVGDQAT-UHFFFAOYSA-N 0.000 description 2
KKVUFSINQFSJNK-UHFFFAOYSA-N o-tert-butylhydroxylamine Chemical compound CC(C)(C)ON KKVUFSINQFSJNK-UHFFFAOYSA-N 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
GAAOKTBHSXYRNH-UHFFFAOYSA-N 2-chloro-n-ethyl-n-[(2-methylphenyl)methyl]ethanamine;hydrochloride Chemical compound [Cl-].ClCC[NH+](CC)CC1=CC=CC=C1C GAAOKTBHSXYRNH-UHFFFAOYSA-N 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
AXTAEHUFZOAUNL-UHFFFAOYSA-N 5-(hydroxyamino)pentanenitrile Chemical compound ONCCCCC#N AXTAEHUFZOAUNL-UHFFFAOYSA-N 0.000 description 1
ISCJLIJIOFOWTR-UHFFFAOYSA-N 5-hydroxypentanenitrile Chemical compound OCCCCC#N ISCJLIJIOFOWTR-UHFFFAOYSA-N 0.000 description 1
229910052695 Americium Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
206010065973 Iron Overload Diseases 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
229910052778 Plutonium Inorganic materials 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
208000031306 Rare hereditary hemochromatosis Diseases 0.000 description 1
239000000589 Siderophore Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
229960001171 acetohydroxamic acid Drugs 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
244000245420 ail Species 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
LXQXZNRPTYVCNG-UHFFFAOYSA-N americium atom Chemical compound [Am] LXQXZNRPTYVCNG-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
OEUUFNIKLCFNLN-LLVKDONJSA-N chembl432481 Chemical compound OC(=O)[C@@]1(C)CSC(C=2C(=CC(O)=CC=2)O)=N1 OEUUFNIKLCFNLN-LLVKDONJSA-N 0.000 description 1
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000039 congener Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
CKHJYUSOUQDYEN-UHFFFAOYSA-N gallium(3+) Chemical compound [Ga+3] CKHJYUSOUQDYEN-UHFFFAOYSA-N 0.000 description 1
235000004611 garlic Nutrition 0.000 description 1
239000003292 glue Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
TWXDDNPPQUTEOV-UHFFFAOYSA-N hydron;n-methyl-1-phenylpropan-2-amine;chloride Chemical class Cl.CNC(C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-UHFFFAOYSA-N 0.000 description 1
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
RSIPQHOWTCNEBI-UHFFFAOYSA-N n-hydroxypropanamide Chemical compound CCC(=O)NO RSIPQHOWTCNEBI-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical class NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
238000010916 retrosynthetic analysis Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229940113082 thymine Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
- C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP15204489A 1988-05-17 1989-06-14 デスフェリオキサミンｂ及びその類似体の合成方法 Pending JPH0334964A (ja)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US352917		1988-05-17
US20631988A	1988-06-14	1988-06-14
US206319		1988-06-14
US24615288A	1988-09-19	1988-09-19
US246152		1988-09-19
US07/352,917 US4987253A (en)	1988-09-19	1989-05-17	Method for the synthesis of desferrioxamine B and analogs thereof

Publications (1)

Publication Number	Publication Date
JPH0334964A true JPH0334964A (ja)	1991-02-14

Family

ID=27394921

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15204489A Pending JPH0334964A (ja)	1988-05-17	1989-06-14	デスフェリオキサミンｂ及びその類似体の合成方法

Country Status (4)

Country	Link
EP (1)	EP0347163A3 (da)
JP (1)	JPH0334964A (da)
DK (1)	DK280389A (da)
PT (1)	PT90838A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2083149C (en) *	1990-07-06	2002-01-01	Peter G. M. Wuts	Intermediate used for the preparation of deferoxamine
US5430176A (en) *	1990-07-06	1995-07-04	The Upjohn Company	Intermediate used for the preparation of deferoxamine
US6858414B2 (en)	1999-12-01	2005-02-22	BIOGAL Gyógyszergyár Rt.	Multistage process for the preparation of highly pure deferoxamine mesylate salt

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK107752C (da) *	1960-10-11	1967-07-03	Ciba Geigy	Fremgangsmåde til fremstilling af trihydroxamsyrer eller salt eller metalkomplekser deraf.
US3810935A (en) *	1970-06-01	1974-05-14	Hoffmann La Roche	Process for producing malononitrile
US3681505A (en) *	1971-04-15	1972-08-01	American Cyanamid Co	Method of controlling insects and acarina with cyanoalkylaldoxime carbamates

1989
- 1989-06-08 DK DK280389A patent/DK280389A/da not_active Application Discontinuation
- 1989-06-12 PT PT9083889A patent/PT90838A/pt not_active Application Discontinuation
- 1989-06-13 EP EP89305951A patent/EP0347163A3/en not_active Ceased
- 1989-06-14 JP JP15204489A patent/JPH0334964A/ja active Pending

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HELV.CHIM.ACTA=1962 *

Also Published As

Publication number	Publication date
DK280389A (da)	1989-12-15
EP0347163A2 (en)	1989-12-20
DK280389D0 (da)	1989-06-08
EP0347163A3 (en)	1990-03-28
PT90838A (pt)	1989-12-29

Publication	Publication Date	Title
US4315007A (en)	1982-02-09	4-Amino-6,7-dimethoxyquinazol-2-yl alkylenediamines
DE69431751T2 (de)	2003-04-03	Benzylaminochinuclidinen mit ein durch ein heteronom substituiertes alkyl als substanz p antagoniste
JP3565843B2 (ja)	2004-09-15	Ｎ−β−ヒドロキシアルキル−トリ−Ｎ−カルボキシアルキル−１，４，７，１０−テトラアザシクロドデカン−及びＮ−β−ヒドロキシアルキル−トリ−Ｎ−カルボキシアルキル−１，４，８，１１−テトラアザシクロテトラデカン−誘導体及びその金属錯体の製法
FR2838439A1 (fr)	2003-10-17	Derives de terphenyle, leur preparation, les compositions pharmaceutqiues en contenant
JPH04507421A (ja)	1992-12-24	５―（１―アミノシクロヘキシル）―２（１ｈ）―ピリジノン及び関連化合物
FR2620121A1 (fr)	1989-03-10	((pyrimidinyl-2)-aminoalkyl)-1 piperidines, leur preparation et leur application en therapeutique
ES2209226T3 (es)	2004-06-16	Derivados de acido fenilaminoalquilcarboxilico y composiciones medicamentosas que los contiienen.
DE68927630T2 (de)	1997-06-12	Analoge von Peptrolsubstraten
US4987253A (en)	1991-01-22	Method for the synthesis of desferrioxamine B and analogs thereof
CH511793A (de)	1971-08-31	Verfahren zur Herstellung von Bornanmethylaminen
DE2600668C2 (de)	1982-03-25	N-(1-Adamantylmethyl)-N'-cinnamylpiperazin, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel
DE69112885T2 (de)	1996-02-15	Zwischenprodukte für Difluoroglutamsäurekonjugate mit Folaten und Antifolaten zur Behandlung von neoplastischen Krankheiten.
JPH0334964A (ja)	1991-02-14	デスフェリオキサミンｂ及びその類似体の合成方法
JP2979054B2 (ja)	1999-11-15	骨関節疾患の治療に有用なｎ−〔｛４，５−ジヒドロキシ−及び４，５，８−トリヒドロキシ−９，１０−ジヒドロ−９，１０−ジオキソ−２−アントラセン−イル｝カルボニル〕アミノ酸
DE69600231T2 (de)	1998-12-17	N-Arylalkylphenylacetamidderivate
Cheng et al.	1990	Synthesis of (1′, 2′-trans)-3-phenyl-1-[2′-(N-pyrrolidinyl) cyclohexyl]-pyrrolid-2-ones as κ-selective opiates
EP1133485B1 (en)	2006-12-20	A process for the synthesis of ritonavir
JP2545105B2 (ja)	1996-10-16	２−アミノ−６，７−ジメトキシテトラリン−ｎ−アルキル誘導体
WO2002059076A1 (de)	2002-08-01	Verfahren zur herstellung von monoamiden der dtpa
JPH0228143A (ja)	1990-01-30	アミド化合物，その製造法ならびにグルタミン酸レセプター阻害剤
DE69306113T2 (de)	1997-03-13	5-amino-2-phenoxysulfonanilid-derivate
DE69621787T2 (de)	2003-02-20	Polyazacycloalkanverbindungen
EP2419431A1 (fr)	2012-02-22	Derives de n-[(7-aza-bicyclo[2.2.1]hept-1-yl)-aryl-methyl]-benzamide, leur preparation et leur application en therapeutique
JPH06500340A (ja)	1994-01-13	新規な第４級アンモニウム塩と、その合成方法と、それを含む医薬
JP2003146957A (ja)	2003-05-21	バリオールアミン製造法およびその中間体